# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_14sab
_database_code_depnum_ccdc_archive 'CCDC 2041133'
loop_
_audit_author_name
_audit_author_address
'Tafeenko Victor'
;Moscow State University (MSU)
Russia
;
_audit_update_record             
;
2020-10-28 deposited with the CCDC.	2021-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H31 Cl N2 Ni'
_chemical_formula_sum            'C30 H31 Cl N2 Ni'
_chemical_formula_weight         513.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   13.6888(4)
_cell_length_b                   10.4380(3)
_cell_length_c                   17.9355(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2562.69(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1653
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      24.2

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .24
_exptl_crystal_size_mid          .21
_exptl_crystal_size_min          .18
_exptl_absorpt_coefficient_mu    0.882

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.371
_exptl_absorpt_correction_T_max  0.707


_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Mo LFF Sealed Tube'
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            39154
_diffrn_reflns_av_unetI/netI     0.1148
_diffrn_reflns_av_R_equivalents  0.1314
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.871
_diffrn_reflns_theta_max         28.253
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6211
_reflns_number_gt                3585
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0164(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1127 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.030(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6211
_refine_ls_number_parameters     314
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   0.881
_refine_ls_restrained_S_all      0.881
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.39143(5) 0.81429(7) 0.43327(4) 0.0397(2) Uani 1 1 d . . . . .
Cl1 Cl 0.34019(13) 0.75619(19) 0.54324(9) 0.0630(5) Uani 1 1 d . . . . .
N1 N 0.3896(3) 0.5427(4) 0.3935(2) 0.0357(10) Uani 1 1 d . . . . .
N2 N 0.2955(3) 0.6543(4) 0.3207(2) 0.0360(11) Uani 1 1 d . . . . .
C1 C 0.3561(4) 0.6653(6) 0.3812(3) 0.0358(13) Uani 1 1 d . . . . .
C3 C 0.5252(6) 0.9193(8) 0.4095(6) 0.079(3) Uani 1 1 d . . . . .
H3 H 0.5890 0.8890 0.4120 0.094 Uiso 1 1 calc R U . . .
C4 C 0.4779(5) 0.9814(7) 0.4636(4) 0.0622(19) Uani 1 1 d . . . . .
H4 H 0.5017 0.9949 0.5115 0.075 Uiso 1 1 calc R U . . .
C5 C 0.3868(6) 1.0232(6) 0.4372(6) 0.083(2) Uani 1 1 d . . . . .
H5 H 0.3409 1.0711 0.4634 0.099 Uiso 1 1 calc R U . . .
C6 C 0.3784(9) 0.9785(9) 0.3634(6) 0.099(3) Uani 1 1 d . . . . .
H6 H 0.3270 0.9926 0.3304 0.119 Uiso 1 1 calc R U . . .
C7 C 0.4643(10) 0.9079(9) 0.3503(5) 0.096(3) Uani 1 1 d . . . . .
H7 H 0.4774 0.8607 0.3075 0.115 Uiso 1 1 calc R U . . .
C8 C 0.2912(4) 0.5285(6) 0.2950(3) 0.0383(13) Uani 1 1 d . . . . .
C9 C 0.2408(4) 0.4736(7) 0.2364(3) 0.0471(15) Uani 1 1 d . . . . .
H9 H 0.1987 0.5212 0.2066 0.056 Uiso 1 1 calc R U . . .
C10 C 0.2558(5) 0.3449(7) 0.2244(4) 0.0551(18) Uani 1 1 d . . . . .
H10 H 0.2237 0.3042 0.1853 0.066 Uiso 1 1 calc R U . . .
C11 C 0.3185(5) 0.2748(6) 0.2698(4) 0.0540(18) Uani 1 1 d . . . . .
H11 H 0.3272 0.1881 0.2600 0.065 Uiso 1 1 calc R U . . .
C12 C 0.3682(4) 0.3288(6) 0.3287(3) 0.0453(14) Uani 1 1 d . . . . .
H12 H 0.4098 0.2811 0.3589 0.054 Uiso 1 1 calc R U . . .
C13 C 0.3525(4) 0.4587(6) 0.3404(3) 0.0365(13) Uani 1 1 d . . . . .
C14 C 0.4474(4) 0.4960(5) 0.4546(3) 0.0375(13) Uani 1 1 d . . . . .
C15 C 0.3997(5) 0.4280(6) 0.5108(3) 0.0464(14) Uani 1 1 d . . . . .
C16 C 0.4567(6) 0.3694(6) 0.5643(4) 0.0630(18) Uani 1 1 d . . . . .
H16 H 0.4264 0.3230 0.6020 0.076 Uiso 1 1 calc R U . . .
C17 C 0.5569(6) 0.3773(7) 0.5636(4) 0.0653(18) Uani 1 1 d . . . . .
C18 C 0.6009(5) 0.4488(7) 0.5080(4) 0.0585(18) Uani 1 1 d . . . . .
H18 H 0.6686 0.4565 0.5080 0.070 Uiso 1 1 calc R U . . .
C19 C 0.5482(4) 0.5091(6) 0.4527(3) 0.0423(14) Uani 1 1 d . . . . .
C20 C 0.5975(4) 0.5822(7) 0.3911(4) 0.0619(17) Uani 1 1 d . . . . .
H20A H 0.5901 0.5365 0.3450 0.093 Uiso 1 1 calc R U . . .
H20B H 0.6657 0.5914 0.4023 0.093 Uiso 1 1 calc R U . . .
H20C H 0.5682 0.6654 0.3866 0.093 Uiso 1 1 calc R U . . .
C21 C 0.6169(7) 0.3095(9) 0.6220(4) 0.100(3) Uani 1 1 d . . . . .
H21A H 0.5898 0.3259 0.6704 0.150 Uiso 1 1 calc R U . . .
H21B H 0.6830 0.3404 0.6202 0.150 Uiso 1 1 calc R U . . .
H21C H 0.6163 0.2190 0.6124 0.150 Uiso 1 1 calc R U . . .
C22 C 0.2896(5) 0.4208(8) 0.5142(4) 0.070(2) Uani 1 1 d . . . . .
H22A H 0.2632 0.5056 0.5190 0.104 Uiso 1 1 calc R U . . .
H22B H 0.2704 0.3701 0.5564 0.104 Uiso 1 1 calc R U . . .
H22C H 0.2653 0.3820 0.4693 0.104 Uiso 1 1 calc R U . . .
C23 C 0.2332(4) 0.7523(6) 0.2908(3) 0.0377(13) Uani 1 1 d . . . . .
C24 C 0.1496(4) 0.7868(5) 0.3297(3) 0.0418(15) Uani 1 1 d . . . . .
C25 C 0.0879(4) 0.8752(6) 0.2964(4) 0.0500(16) Uani 1 1 d . . . . .
H25 H 0.0317 0.9001 0.3217 0.060 Uiso 1 1 calc R U . . .
C26 C 0.1064(5) 0.9275(7) 0.2276(4) 0.0581(17) Uani 1 1 d . . . . .
C27 C 0.1895(5) 0.8889(7) 0.1905(4) 0.0546(18) Uani 1 1 d . . . . .
H27 H 0.2025 0.9236 0.1437 0.065 Uiso 1 1 calc R U . . .
C28 C 0.2547(4) 0.8006(7) 0.2199(3) 0.0460(15) Uani 1 1 d . . . . .
C29 C 0.3451(5) 0.7583(7) 0.1774(3) 0.0613(18) Uani 1 1 d . . . . .
H29A H 0.3445 0.7956 0.1285 0.092 Uiso 1 1 calc R U . . .
H29B H 0.3455 0.6666 0.1732 0.092 Uiso 1 1 calc R U . . .
H29C H 0.4025 0.7858 0.2036 0.092 Uiso 1 1 calc R U . . .
C30 C 0.0370(6) 1.0225(9) 0.1925(5) 0.086(3) Uani 1 1 d . . . . .
H30A H 0.0717 1.0741 0.1570 0.129 Uiso 1 1 calc R U . . .
H30B H 0.0099 1.0766 0.2305 0.129 Uiso 1 1 calc R U . . .
H30C H -0.0147 0.9772 0.1677 0.129 Uiso 1 1 calc R U . . .
C31 C 0.1257(4) 0.7296(6) 0.4041(3) 0.0502(16) Uani 1 1 d . . . . .
H31A H 0.1360 0.6386 0.4024 0.075 Uiso 1 1 calc R U . . .
H31B H 0.0587 0.7468 0.4161 0.075 Uiso 1 1 calc R U . . .
H31C H 0.1672 0.7666 0.4415 0.075 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 C1 1.877(6) . ?
Ni1 C7 2.041(8) . ?
Ni1 C6 2.131(7) . ?
Ni1 C3 2.176(7) . ?
Ni1 C4 2.177(6) . ?
Ni1 Cl1 2.1796(17) . ?
Ni1 C5 2.183(6) . ?
N1 C1 1.377(7) . ?
N1 C13 1.391(7) . ?
N1 C14 1.437(7) . ?
N2 C1 1.371(6) . ?
N2 C8 1.393(7) . ?
N2 C23 1.436(7) . ?
C3 C4 1.334(10) . ?
C3 C7 1.355(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.404(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.408(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.409(13) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.377(7) . ?
C8 C9 1.382(8) . ?
C9 C10 1.376(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.391(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(8) . ?
C12 H12 0.9300 . ?
C14 C19 1.387(7) . ?
C14 C15 1.393(7) . ?
C15 C16 1.380(9) . ?
C15 C22 1.510(9) . ?
C16 C17 1.373(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.383(10) . ?
C17 C21 1.508(10) . ?
C18 C19 1.379(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.504(9) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.387(8) . ?
C23 C28 1.400(8) . ?
C24 C25 1.387(8) . ?
C24 C31 1.498(8) . ?
C25 C26 1.373(9) . ?
C25 H25 0.9300 . ?
C26 C27 1.378(9) . ?
C26 C30 1.511(9) . ?
C27 C28 1.387(9) . ?
C27 H27 0.9300 . ?
C28 C29 1.519(9) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ni1 C7 99.2(3) . . ?
C1 Ni1 C6 110.6(3) . . ?
C7 Ni1 C6 39.4(4) . . ?
C1 Ni1 C3 122.5(3) . . ?
C7 Ni1 C3 37.3(3) . . ?
C6 Ni1 C3 63.3(4) . . ?
C1 Ni1 C4 158.1(3) . . ?
C7 Ni1 C4 62.1(3) . . ?
C6 Ni1 C4 63.1(3) . . ?
C3 Ni1 C4 35.7(3) . . ?
C1 Ni1 Cl1 97.84(16) . . ?
C7 Ni1 Cl1 161.9(3) . . ?
C6 Ni1 Cl1 136.8(4) . . ?
C3 Ni1 Cl1 126.0(3) . . ?
C4 Ni1 Cl1 99.9(2) . . ?
C1 Ni1 C5 146.8(3) . . ?
C7 Ni1 C5 63.9(4) . . ?
C6 Ni1 C5 38.1(3) . . ?
C3 Ni1 C5 61.8(3) . . ?
C4 Ni1 C5 37.6(3) . . ?
Cl1 Ni1 C5 103.8(3) . . ?
C1 N1 C13 110.8(4) . . ?
C1 N1 C14 128.4(4) . . ?
C13 N1 C14 120.6(4) . . ?
C1 N2 C8 111.5(5) . . ?
C1 N2 C23 126.6(5) . . ?
C8 N2 C23 121.5(4) . . ?
N2 C1 N1 104.5(5) . . ?
N2 C1 Ni1 128.2(4) . . ?
N1 C1 Ni1 127.2(4) . . ?
C4 C3 C7 108.3(8) . . ?
C4 C3 Ni1 72.2(4) . . ?
C7 C3 Ni1 65.9(4) . . ?
C4 C3 H3 125.8 . . ?
C7 C3 H3 125.8 . . ?
Ni1 C3 H3 127.6 . . ?
C3 C4 C5 109.7(7) . . ?
C3 C4 Ni1 72.1(4) . . ?
C5 C4 Ni1 71.4(4) . . ?
C3 C4 H4 125.1 . . ?
C5 C4 H4 125.1 . . ?
Ni1 C4 H4 122.9 . . ?
C4 C5 C6 106.6(8) . . ?
C4 C5 Ni1 71.0(4) . . ?
C6 C5 Ni1 69.0(4) . . ?
C4 C5 H5 126.7 . . ?
C6 C5 H5 126.7 . . ?
Ni1 C5 H5 125.0 . . ?
C5 C6 C7 105.2(7) . . ?
C5 C6 Ni1 73.0(4) . . ?
C7 C6 Ni1 66.9(4) . . ?
C5 C6 H6 127.4 . . ?
C7 C6 H6 127.4 . . ?
Ni1 C6 H6 124.4 . . ?
C3 C7 C6 109.7(8) . . ?
C3 C7 Ni1 76.8(5) . . ?
C6 C7 Ni1 73.7(5) . . ?
C3 C7 H7 125.2 . . ?
C6 C7 H7 125.2 . . ?
Ni1 C7 H7 116.2 . . ?
C13 C8 C9 122.3(6) . . ?
C13 C8 N2 106.1(5) . . ?
C9 C8 N2 131.6(6) . . ?
C10 C9 C8 116.7(6) . . ?
C10 C9 H9 121.6 . . ?
C8 C9 H9 121.6 . . ?
C9 C10 C11 120.9(6) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 122.6(6) . . ?
C12 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C11 C12 C13 116.0(6) . . ?
C11 C12 H12 122.0 . . ?
C13 C12 H12 122.0 . . ?
C8 C13 C12 121.4(5) . . ?
C8 C13 N1 107.1(5) . . ?
C12 C13 N1 131.5(5) . . ?
C19 C14 C15 122.2(5) . . ?
C19 C14 N1 119.7(5) . . ?
C15 C14 N1 117.8(5) . . ?
C16 C15 C14 117.6(6) . . ?
C16 C15 C22 120.9(6) . . ?
C14 C15 C22 121.4(6) . . ?
C17 C16 C15 122.1(7) . . ?
C17 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
C16 C17 C18 118.3(6) . . ?
C16 C17 C21 120.6(8) . . ?
C18 C17 C21 121.0(7) . . ?
C19 C18 C17 122.4(6) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C18 C19 C14 117.3(6) . . ?
C18 C19 C20 121.7(5) . . ?
C14 C19 C20 121.0(5) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C15 C22 H22A 109.5 . . ?
C15 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C15 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 122.5(5) . . ?
C24 C23 N2 119.2(5) . . ?
C28 C23 N2 118.1(5) . . ?
C23 C24 C25 117.4(5) . . ?
C23 C24 C31 121.6(5) . . ?
C25 C24 C31 121.0(5) . . ?
C26 C25 C24 122.6(6) . . ?
C26 C25 H25 118.7 . . ?
C24 C25 H25 118.7 . . ?
C25 C26 C27 118.1(6) . . ?
C25 C26 C30 121.3(7) . . ?
C27 C26 C30 120.6(6) . . ?
C26 C27 C28 122.8(6) . . ?
C26 C27 H27 118.6 . . ?
C28 C27 H27 118.6 . . ?
C27 C28 C23 116.7(6) . . ?
C27 C28 C29 121.8(6) . . ?
C23 C28 C29 121.5(6) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C26 C30 H30A 109.5 . . ?
C26 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C26 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C24 C31 H31A 109.5 . . ?
C24 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C24 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N2 C1 N1 -0.4(5) . . . . ?
C23 N2 C1 N1 172.1(5) . . . . ?
C8 N2 C1 Ni1 176.7(4) . . . . ?
C23 N2 C1 Ni1 -10.8(7) . . . . ?
C13 N1 C1 N2 1.6(5) . . . . ?
C14 N1 C1 N2 -172.9(4) . . . . ?
C13 N1 C1 Ni1 -175.6(4) . . . . ?
C14 N1 C1 Ni1 10.0(7) . . . . ?
C7 Ni1 C1 N2 -63.9(6) . . . . ?
C6 Ni1 C1 N2 -24.8(6) . . . . ?
C3 Ni1 C1 N2 -95.5(5) . . . . ?
C4 Ni1 C1 N2 -93.8(8) . . . . ?
Cl1 Ni1 C1 N2 122.2(4) . . . . ?
C5 Ni1 C1 N2 -8.4(7) . . . . ?
C7 Ni1 C1 N1 112.6(6) . . . . ?
C6 Ni1 C1 N1 151.7(6) . . . . ?
C3 Ni1 C1 N1 81.0(6) . . . . ?
C4 Ni1 C1 N1 82.7(8) . . . . ?
Cl1 Ni1 C1 N1 -61.3(4) . . . . ?
C5 Ni1 C1 N1 168.1(5) . . . . ?
C7 C3 C4 C5 -5.8(9) . . . . ?
Ni1 C3 C4 C5 -61.9(5) . . . . ?
C7 C3 C4 Ni1 56.1(6) . . . . ?
C3 C4 C5 C6 2.3(8) . . . . ?
Ni1 C4 C5 C6 -60.0(5) . . . . ?
C3 C4 C5 Ni1 62.4(5) . . . . ?
C4 C5 C6 C7 2.0(8) . . . . ?
Ni1 C5 C6 C7 -59.4(5) . . . . ?
C4 C5 C6 Ni1 61.4(5) . . . . ?
C4 C3 C7 C6 7.1(10) . . . . ?
Ni1 C3 C7 C6 67.1(6) . . . . ?
C4 C3 C7 Ni1 -59.9(6) . . . . ?
C5 C6 C7 C3 -5.6(9) . . . . ?
Ni1 C6 C7 C3 -69.0(6) . . . . ?
C5 C6 C7 Ni1 63.5(5) . . . . ?
C1 N2 C8 C13 -0.9(6) . . . . ?
C23 N2 C8 C13 -173.9(5) . . . . ?
C1 N2 C8 C9 -179.8(6) . . . . ?
C23 N2 C8 C9 7.2(9) . . . . ?
C13 C8 C9 C10 -1.2(8) . . . . ?
N2 C8 C9 C10 177.6(6) . . . . ?
C8 C9 C10 C11 0.5(9) . . . . ?
C9 C10 C11 C12 0.2(9) . . . . ?
C10 C11 C12 C13 -0.2(8) . . . . ?
C9 C8 C13 C12 1.2(8) . . . . ?
N2 C8 C13 C12 -177.8(5) . . . . ?
C9 C8 C13 N1 -179.1(5) . . . . ?
N2 C8 C13 N1 1.9(6) . . . . ?
C11 C12 C13 C8 -0.5(8) . . . . ?
C11 C12 C13 N1 179.9(5) . . . . ?
C1 N1 C13 C8 -2.2(6) . . . . ?
C14 N1 C13 C8 172.8(4) . . . . ?
C1 N1 C13 C12 177.4(6) . . . . ?
C14 N1 C13 C12 -7.6(8) . . . . ?
C1 N1 C14 C19 -83.9(7) . . . . ?
C13 N1 C14 C19 102.0(6) . . . . ?
C1 N1 C14 C15 101.9(7) . . . . ?
C13 N1 C14 C15 -72.1(6) . . . . ?
C19 C14 C15 C16 -2.1(9) . . . . ?
N1 C14 C15 C16 171.9(5) . . . . ?
C19 C14 C15 C22 176.7(6) . . . . ?
N1 C14 C15 C22 -9.4(9) . . . . ?
C14 C15 C16 C17 0.5(10) . . . . ?
C22 C15 C16 C17 -178.3(7) . . . . ?
C15 C16 C17 C18 1.3(10) . . . . ?
C15 C16 C17 C21 -178.6(6) . . . . ?
C16 C17 C18 C19 -1.7(10) . . . . ?
C21 C17 C18 C19 178.2(6) . . . . ?
C17 C18 C19 C14 0.2(9) . . . . ?
C17 C18 C19 C20 -177.6(6) . . . . ?
C15 C14 C19 C18 1.7(9) . . . . ?
N1 C14 C19 C18 -172.1(5) . . . . ?
C15 C14 C19 C20 179.5(6) . . . . ?
N1 C14 C19 C20 5.7(8) . . . . ?
C1 N2 C23 C24 -72.4(7) . . . . ?
C8 N2 C23 C24 99.4(6) . . . . ?
C1 N2 C23 C28 113.4(6) . . . . ?
C8 N2 C23 C28 -74.7(7) . . . . ?
C28 C23 C24 C25 -1.7(9) . . . . ?
N2 C23 C24 C25 -175.6(5) . . . . ?
C28 C23 C24 C31 177.3(5) . . . . ?
N2 C23 C24 C31 3.4(8) . . . . ?
C23 C24 C25 C26 0.4(9) . . . . ?
C31 C24 C25 C26 -178.6(6) . . . . ?
C24 C25 C26 C27 0.5(10) . . . . ?
C24 C25 C26 C30 179.3(7) . . . . ?
C25 C26 C27 C28 -0.3(10) . . . . ?
C30 C26 C27 C28 -179.0(7) . . . . ?
C26 C27 C28 C23 -0.9(9) . . . . ?
C26 C27 C28 C29 179.1(6) . . . . ?
C24 C23 C28 C27 1.9(9) . . . . ?
N2 C23 C28 C27 175.9(5) . . . . ?
C24 C23 C28 C29 -178.1(6) . . . . ?
N2 C23 C28 C29 -4.1(8) . . . . ?

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.148



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ShKAct145
_database_code_depnum_ccdc_archive 'CCDC 2041290'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2020-10-29 deposited with the CCDC.	2021-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
7-(1-phenylethyl)-2-(pyridin-3-yl)[1,2,4]triazolo[1,5-a]pyrimidine
_chemical_name_common            ?
_chemical_melting_point          392
_chemical_formula_moiety         'C18 H15 N5'
_chemical_formula_sum            'C18 H15 N5'
_chemical_formula_weight         301.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.0740(3)
_cell_length_b                   11.5334(3)
_cell_length_c                   12.8541(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.0366(6)
_cell_angle_gamma                90
_cell_volume                     1489.78(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9895
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      37.75

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.45
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8157
_exptl_absorpt_correction_T_max  0.8626
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-Ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            50812
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.688
_diffrn_reflns_theta_max         37.038
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7589
_reflns_number_gt                6270
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    
'SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0572P)²+0.3537P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7589
_refine_ls_number_parameters     248
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.61469(6) 0.49686(5) 0.61028(4) 0.01416(10) Uani 1 1 d . . . . .
N2 N 0.69020(6) 0.56156(5) 0.54851(5) 0.01517(10) Uani 1 1 d . . . . .
N3 N 0.51439(6) 0.66822(5) 0.60032(5) 0.01641(10) Uani 1 1 d . . . . .
N4 N 0.41917(6) 0.51984(6) 0.70420(5) 0.01866(11) Uani 1 1 d . . . . .
N5 N 0.64680(7) 0.95909(6) 0.43019(5) 0.02085(12) Uani 1 1 d . . . . .
C1 C 0.62484(6) 0.66280(6) 0.54559(5) 0.01451(11) Uani 1 1 d . . . . .
C2 C 0.50891(7) 0.56225(6) 0.64140(5) 0.01528(11) Uani 1 1 d . . . . .
C3 C 0.43957(7) 0.41079(7) 0.73329(6) 0.01929(12) Uani 1 1 d . . . . .
H3 H 0.3761(8) 0.3760(4) 0.7803(6) 0.023 Uiso 1 1 calc R U . . .
C4 C 0.54451(7) 0.33994(6) 0.70276(5) 0.01809(12) Uani 1 1 d . . . . .
H4 H 0.55193(12) 0.2602(10) 0.7269(3) 0.022 Uiso 1 1 calc R U . . .
C5 C 0.63575(7) 0.38386(6) 0.63910(5) 0.01529(11) Uani 1 1 d D . . . .
C6 C 0.67122(7) 0.75986(6) 0.48424(5) 0.01508(11) Uani 1 1 d . . . . .
C7 C 0.60943(7) 0.86824(6) 0.48605(6) 0.01697(11) Uani 1 1 d . . . . .
H7 H 0.5367(9) 0.87804(14) 0.5294(5) 0.020 Uiso 1 1 calc R U . . .
C8 C 0.74873(8) 0.94309(7) 0.36998(6) 0.02276(14) Uani 1 1 d . . . . .
H8 H 0.7778(4) 1.0096(9) 0.3285(6) 0.027 Uiso 1 1 calc R U . . .
C9 C 0.81587(8) 0.83860(7) 0.36247(6) 0.02308(14) Uani 1 1 d . . . . .
H9 H 0.8878(10) 0.83125(12) 0.3180(6) 0.028 Uiso 1 1 calc R U . . .
C10 C 0.77659(7) 0.74523(7) 0.42075(6) 0.01961(12) Uani 1 1 d . . . . .
H10 H 0.8233(6) 0.6681(9) 0.41730(7) 0.024 Uiso 1 1 calc R U . . .
C11A C 0.75896(7) 0.32460(7) 0.60424(6) 0.01562(13) Uani 0.9465(18) 1 d D . P A
1
H11A H 0.7844(3) 0.3635(5) 0.5392(8) 0.019 Uiso 0.9465(18) 1 calc R U P A 1
C12A C 0.87081(11) 0.34481(11) 0.68936(7) 0.01676(16) Uani 0.9465(18) 1 d D . P
A 1
C13A C 0.96428(9) 0.43153(8) 0.67618(8) 0.02022(16) Uani 0.9465(18) 1 d D . P A
1
H13A H 0.95959(11) 0.4781(7) 0.6106(9) 0.024 Uiso 0.9465(18) 1 calc R U P A 1
C14A C 1.06450(9) 0.45371(9) 0.75418(9) 0.02502(18) Uani 0.9465(18) 1 d D . P A
1
H1A H 1.1302(10) 0.5144(9) 0.74418(18) 0.030 Uiso 0.9465(18) 1 calc R U P A 1
C15A C 1.07114(9) 0.38987(9) 0.84585(9) 0.02668(18) Uani 0.9465(18) 1 d D . P A
1
H15A H 1.1399(10) 0.4058(3) 0.8999(8) 0.032 Uiso 0.9465(18) 1 calc R U P A 1
C16A C 0.97827(10) 0.30279(9) 0.85969(8) 0.02488(17) Uani 0.9465(18) 1 d D . P
A 1
H16A H 0.98352(12) 0.2564(7) 0.9250(9) 0.030 Uiso 0.9465(18) 1 calc R U P A 1
C17A C 0.87804(9) 0.28067(8) 0.78203(7) 0.02025(15) Uani 0.9465(18) 1 d D . P A
1
H17A H 0.8116(9) 0.2193(9) 0.79241(16) 0.024 Uiso 0.9465(18) 1 calc R U P A 1
C18A C 0.73643(8) 0.19562(7) 0.58019(7) 0.02092(15) Uani 0.9465(18) 1 d D . P A
1
H18A H 0.7001(8) 0.1573(3) 0.6408(6) 0.031 Uiso 0.9465(18) 1 calc R U P A 1
H18B H 0.8219(7) 0.1591(3) 0.5658(6) 0.031 Uiso 0.9465(18) 1 calc R U P A 1
H18C H 0.6728(8) 0.18739(10) 0.5185(6) 0.031 Uiso 0.9465(18) 1 calc R U P A 1
C11B C 0.7466(10) 0.2991(10) 0.6225(9) 0.01562(13) Uani 0.0535(18) 1 d D . P A
2
H11B H 0.728641 0.219965 0.650062 0.019 Uiso 0.0535(18) 1 calc R U P A 2
C12B C 0.876(2) 0.352(2) 0.6715(16) 0.01676(16) Uani 0.0535(18) 1 d D . P A 2
C13B C 0.9623(16) 0.4409(16) 0.6477(14) 0.02022(16) Uani 0.0535(18) 1 d D . P A
2
H13B H 0.947174 0.483101 0.584564 0.024 Uiso 0.0535(18) 1 calc R U P A 2
C14B C 1.0712(16) 0.4679(16) 0.7166(13) 0.02502(18) Uani 0.0535(18) 1 d D . P A
2
H14B H 1.132657 0.525555 0.698190 0.030 Uiso 0.0535(18) 1 calc R U P A 2
C15B C 1.0903(17) 0.4114(14) 0.8116(14) 0.02668(18) Uani 0.0535(18) 1 d D . P A
2
H15B H 1.158573 0.437077 0.860979 0.032 Uiso 0.0535(18) 1 calc R U P A 2
C16B C 1.0114(16) 0.3176(14) 0.8357(13) 0.02488(17) Uani 0.0535(18) 1 d D . P A
2
H16B H 1.027373 0.275162 0.898744 0.030 Uiso 0.0535(18) 1 calc R U P A 2
C17B C 0.9075(16) 0.2889(16) 0.7628(12) 0.02025(15) Uani 0.0535(18) 1 d D . P A
2
H17B H 0.855245 0.222658 0.775938 0.024 Uiso 0.0535(18) 1 calc R U P A 2
C18B C 0.7746(14) 0.2982(12) 0.5070(9) 0.02092(15) Uani 0.0535(18) 1 d D . P A
2
H18D H 0.691021 0.287350 0.464343 0.031 Uiso 0.0535(18) 1 calc R U P A 2
H18E H 0.835717 0.234592 0.493849 0.031 Uiso 0.0535(18) 1 calc R U P A 2
H18F H 0.815071 0.372109 0.488836 0.031 Uiso 0.0535(18) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.3605(8) . ?
N1 C5 1.3674(9) . ?
N1 C2 1.3872(9) . ?
N2 C1 1.3397(9) . ?
N3 C2 1.3340(9) . ?
N3 C1 1.3592(9) . ?
N4 C3 1.3240(10) . ?
N4 C2 1.3458(9) . ?
N5 C7 1.3392(9) . ?
N5 C8 1.3414(11) . ?
C1 C6 1.4646(9) . ?
C3 C4 1.4134(11) . ?
C3 H3 0.994(12) . ?
C4 C5 1.3700(10) . ?
C4 H4 0.971(12) . ?
C5 C11B 1.510(3) . ?
C5 C11A 1.5122(10) . ?
C6 C10 1.3940(10) . ?
C6 C7 1.3973(10) . ?
C7 H7 0.958(12) . ?
C8 C9 1.3886(12) . ?
C8 H8 0.991(13) . ?
C9 C10 1.3853(11) . ?
C9 H9 0.958(13) . ?
C10 H10 1.008(12) . ?
C11A C12A 1.5322(10) . ?
C11A C18A 1.5330(11) . ?
C11A H11A 0.998(13) . ?
C12A C13A 1.3922(11) . ?
C12A C17A 1.3997(12) . ?
C13A C14A 1.3955(13) . ?
C13A H13A 0.998(14) . ?
C14A C15A 1.3871(15) . ?
C14A H1A 0.978(15) . ?
C15A C16A 1.3925(15) . ?
C15A H15A 0.964(14) . ?
C16A C17A 1.3926(11) . ?
C16A H16A 0.994(14) . ?
C17A H17A 0.990(14) . ?
C18A H18A 0.988(8) . ?
C18A H18B 0.988(8) . ?
C18A H18C 0.988(8) . ?
C11B C18B 1.531(3) . ?
C11B C12B 1.533(3) . ?
C11B H11B 1.0000 . ?
C12B C13B 1.393(3) . ?
C12B C17B 1.399(3) . ?
C13B C14B 1.395(3) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.386(3) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.391(3) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.394(3) . ?
C16B H16B 0.9500 . ?
C17B H17B 0.9500 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C5 126.76(6) . . ?
N2 N1 C2 110.03(5) . . ?
C5 N1 C2 123.21(6) . . ?
C1 N2 N1 101.57(5) . . ?
C2 N3 C1 102.76(6) . . ?
C3 N4 C2 114.66(6) . . ?
C7 N5 C8 117.21(7) . . ?
N2 C1 N3 116.37(6) . . ?
N2 C1 C6 120.43(6) . . ?
N3 C1 C6 123.19(6) . . ?
N3 C2 N4 128.22(6) . . ?
N3 C2 N1 109.26(6) . . ?
N4 C2 N1 122.52(6) . . ?
N4 C3 C4 125.10(7) . . ?
N4 C3 H3 117.4 . . ?
C4 C3 H3 117.4 . . ?
C5 C4 C3 119.90(7) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N1 C5 C4 114.61(6) . . ?
N1 C5 C11B 132.9(5) . . ?
C4 C5 C11B 112.2(5) . . ?
N1 C5 C11A 117.74(6) . . ?
C4 C5 C11A 127.52(7) . . ?
C10 C6 C7 118.46(6) . . ?
C10 C6 C1 120.51(6) . . ?
C7 C6 C1 121.02(6) . . ?
N5 C7 C6 123.27(7) . . ?
N5 C7 H7 118.4 . . ?
C6 C7 H7 118.4 . . ?
N5 C8 C9 123.77(7) . . ?
N5 C8 H8 118.1 . . ?
C9 C8 H8 118.1 . . ?
C10 C9 C8 118.56(7) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C9 C10 C6 118.73(7) . . ?
C9 C10 H10 120.6 . . ?
C6 C10 H10 120.6 . . ?
C5 C11A C12A 107.30(7) . . ?
C5 C11A C18A 112.67(6) . . ?
C12A C11A C18A 112.50(8) . . ?
C5 C11A H11A 108.1 . . ?
C12A C11A H11A 108.1 . . ?
C18A C11A H11A 108.1 . . ?
C13A C12A C17A 119.22(8) . . ?
C13A C12A C11A 119.48(8) . . ?
C17A C12A C11A 121.26(8) . . ?
C12A C13A C14A 120.37(8) . . ?
C12A C13A H13A 119.8 . . ?
C14A C13A H13A 119.8 . . ?
C15A C14A C13A 120.15(8) . . ?
C15A C14A H1A 119.9 . . ?
C13A C14A H1A 119.9 . . ?
C14A C15A C16A 119.92(8) . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C15A C16A C17A 120.02(9) . . ?
C15A C16A H16A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C16A C17A C12A 120.33(9) . . ?
C16A C17A H17A 119.8 . . ?
C12A C17A H17A 119.8 . . ?
C11A C18A H18A 109.5 . . ?
C11A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C11A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C5 C11B C18B 109.3(8) . . ?
C5 C11B C12B 107.4(14) . . ?
C18B C11B C12B 101.0(13) . . ?
C5 C11B H11B 112.8 . . ?
C18B C11B H11B 112.8 . . ?
C12B C11B H11B 112.8 . . ?
C13B C12B C17B 117.2(14) . . ?
C13B C12B C11B 136.8(13) . . ?
C17B C12B C11B 105.9(10) . . ?
C12B C13B C14B 120.1(15) . . ?
C12B C13B H13B 120.0 . . ?
C14B C13B H13B 120.0 . . ?
C15B C14B C13B 120.6(16) . . ?
C15B C14B H14B 119.7 . . ?
C13B C14B H14B 119.7 . . ?
C14B C15B C16B 121.1(15) . . ?
C14B C15B H15B 119.5 . . ?
C16B C15B H15B 119.5 . . ?
C15B C16B C17B 116.6(15) . . ?
C15B C16B H16B 121.7 . . ?
C17B C16B H16B 121.7 . . ?
C16B C17B C12B 123.9(15) . . ?
C16B C17B H17B 118.1 . . ?
C12B C17B H17B 118.1 . . ?
C11B C18B H18D 109.5 . . ?
C11B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C11B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 C1 179.51(6) . . . . ?
C2 N1 N2 C1 -0.23(7) . . . . ?
N1 N2 C1 N3 0.12(8) . . . . ?
N1 N2 C1 C6 -178.72(6) . . . . ?
C2 N3 C1 N2 0.04(8) . . . . ?
C2 N3 C1 C6 178.85(6) . . . . ?
C1 N3 C2 N4 179.23(7) . . . . ?
C1 N3 C2 N1 -0.19(7) . . . . ?
C3 N4 C2 N3 -179.72(7) . . . . ?
C3 N4 C2 N1 -0.36(10) . . . . ?
N2 N1 C2 N3 0.28(8) . . . . ?
C5 N1 C2 N3 -179.47(6) . . . . ?
N2 N1 C2 N4 -179.18(6) . . . . ?
C5 N1 C2 N4 1.06(10) . . . . ?
C2 N4 C3 C4 -0.53(11) . . . . ?
N4 C3 C4 C5 0.78(12) . . . . ?
N2 N1 C5 C4 179.52(6) . . . . ?
C2 N1 C5 C4 -0.77(10) . . . . ?
N2 N1 C5 C11B 5.6(6) . . . . ?
C2 N1 C5 C11B -174.7(6) . . . . ?
N2 N1 C5 C11A 3.40(10) . . . . ?
C2 N1 C5 C11A -176.89(6) . . . . ?
C3 C4 C5 N1 -0.09(10) . . . . ?
C3 C4 C5 C11B 175.1(5) . . . . ?
C3 C4 C5 C11A 175.58(7) . . . . ?
N2 C1 C6 C10 5.76(10) . . . . ?
N3 C1 C6 C10 -172.99(7) . . . . ?
N2 C1 C6 C7 -175.66(6) . . . . ?
N3 C1 C6 C7 5.59(10) . . . . ?
C8 N5 C7 C6 0.10(11) . . . . ?
C10 C6 C7 N5 -0.35(11) . . . . ?
C1 C6 C7 N5 -178.96(7) . . . . ?
C7 N5 C8 C9 0.30(12) . . . . ?
N5 C8 C9 C10 -0.44(13) . . . . ?
C8 C9 C10 C6 0.16(12) . . . . ?
C7 C6 C10 C9 0.20(11) . . . . ?
C1 C6 C10 C9 178.82(7) . . . . ?
N1 C5 C11A C12A 90.16(8) . . . . ?
C4 C5 C11A C12A -85.39(9) . . . . ?
N1 C5 C11A C18A -145.48(7) . . . . ?
C4 C5 C11A C18A 38.97(10) . . . . ?
C5 C11A C12A C13A -99.79(12) . . . . ?
C18A C11A C12A C13A 135.75(11) . . . . ?
C5 C11A C12A C17A 77.77(13) . . . . ?
C18A C11A C12A C17A -46.69(14) . . . . ?
C17A C12A C13A C14A 0.41(17) . . . . ?
C11A C12A C13A C14A 178.02(9) . . . . ?
C12A C13A C14A C15A -0.43(15) . . . . ?
C13A C14A C15A C16A 0.56(14) . . . . ?
C14A C15A C16A C17A -0.67(14) . . . . ?
C15A C16A C17A C12A 0.66(15) . . . . ?
C13A C12A C17A C16A -0.53(17) . . . . ?
C11A C12A C17A C16A -178.09(10) . . . . ?
N1 C5 C11B C18B -49.9(12) . . . . ?
C4 C5 C11B C18B 136.1(8) . . . . ?
N1 C5 C11B C12B 58.9(11) . . . . ?
C4 C5 C11B C12B -115.1(9) . . . . ?
C5 C11B C12B C13B -74(4) . . . . ?
C18B C11B C12B C13B 41(4) . . . . ?
C5 C11B C12B C17B 107(2) . . . . ?
C18B C11B C12B C17B -138.9(19) . . . . ?
C17B C12B C13B C14B -3(4) . . . . ?
C11B C12B C13B C14B 177(3) . . . . ?
C12B C13B C14B C15B -4(3) . . . . ?
C13B C14B C15B C16B 8(3) . . . . ?
C14B C15B C16B C17B -4(3) . . . . ?
C15B C16B C17B C12B -3(3) . . . . ?
C13B C12B C17B C16B 7(4) . . . . ?
C11B C12B C17B C16B -173.3(18) . . . . ?

_refine_diff_density_max         0.496
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.052



_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ShKAct144
_database_code_depnum_ccdc_archive 'CCDC 2041286'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2020-10-29 deposited with the CCDC.	2021-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
7-[1-(4-methylphenyl)ethyl]-2-(thiophen-2-yl)[1,2,4]triazolo[1,5-a]pyrimidine
_chemical_name_common            ?
_chemical_melting_point          432
_chemical_formula_moiety         'C18 H16 N4 S'
_chemical_formula_sum            'C18 H16 N4 S'
_chemical_formula_weight         320.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.7847(2)
_cell_length_b                   11.4013(2)
_cell_length_c                   11.9092(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.6061(6)
_cell_angle_gamma                90
_cell_volume                     1600.04(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      33.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6975
_exptl_absorpt_correction_T_max  0.7477
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-Ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            83334
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.473
_diffrn_reflns_theta_max         37.039
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8158
_reflns_number_gt                4963
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    
'SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0552P)²+0.8249P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8158
_refine_ls_number_parameters     227
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1608
_refine_ls_wR_factor_gt          0.1301
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.88613(9) 0.49678(9) 0.40549(9) 0.0210(2) Uani 1 1 d . . . . .
N2 N 0.81889(10) 0.55450(9) 0.47969(9) 0.0233(2) Uani 1 1 d . . . . .
C1 C 0.86349(11) 0.66249(11) 0.47758(11) 0.0234(2) Uani 1 1 d D . . . .
N3 N 0.95341(10) 0.67876(10) 0.40836(9) 0.0242(2) Uani 1 1 d . . . . .
C2 C 0.96697(11) 0.57278(11) 0.36277(11) 0.0225(2) Uani 1 1 d . . . . .
N4 N 1.04386(10) 0.53785(10) 0.28737(10) 0.0257(2) Uani 1 1 d . . . . .
C3 C 1.03658(12) 0.42607(12) 0.25756(11) 0.0261(3) Uani 1 1 d . . . . .
H3 H 1.089536 0.398049 0.204289 0.031 Uiso 1 1 calc R U . . .
C4 C 0.95635(12) 0.34550(11) 0.29877(11) 0.0250(2) Uani 1 1 d . . . . .
H4 H 0.956502 0.266520 0.273339 0.030 Uiso 1 1 calc R U . . .
C5 C 0.87816(11) 0.38181(11) 0.37571(11) 0.0222(2) Uani 1 1 d . . . . .
C6A C 0.8159(6) 0.7501(2) 0.5520(5) 0.0224(5) Uani 0.699(2) 1 d D . P A 1
S1A S 0.86377(9) 0.89396(5) 0.54670(9) 0.02608(16) Uani 0.699(2) 1 d D . P A 1
C7A C 0.7690(3) 0.9354(4) 0.6481(3) 0.0279(6) Uani 0.699(2) 1 d D . P A 1
H7A H 0.762296 1.013226 0.675668 0.034 Uiso 0.699(2) 1 calc R U P A 1
C8A C 0.7047(4) 0.8442(2) 0.6845(4) 0.0327(5) Uani 0.699(2) 1 d D . P A 1
H8A H 0.649813 0.849400 0.742209 0.039 Uiso 0.699(2) 1 calc R U P A 1
C9A C 0.7313(7) 0.7383(9) 0.6234(8) 0.0376(5) Uani 0.699(2) 1 d D . P A 1
H9A H 0.691608 0.666666 0.633598 0.045 Uiso 0.699(2) 1 calc R U P A 1
C6B C 0.8207(14) 0.7625(4) 0.5397(13) 0.0224(5) Uani 0.301(2) 1 d D . P A 2
S1B S 0.7141(4) 0.7284(5) 0.6337(4) 0.0376(5) Uani 0.301(2) 1 d D . P A 2
C7B C 0.7123(11) 0.8719(5) 0.6782(11) 0.0327(5) Uani 0.301(2) 1 d D . P A 2
H7B H 0.659575 0.901915 0.730637 0.039 Uiso 0.301(2) 1 calc R U P A 2
C8B C 0.7949(8) 0.9374(10) 0.6299(9) 0.0279(6) Uani 0.301(2) 1 d D . P A 2
H8B H 0.808154 1.017873 0.646195 0.034 Uiso 0.301(2) 1 calc R U P A 2
C9B C 0.8587(11) 0.8710(6) 0.5521(10) 0.02608(16) Uani 0.301(2) 1 d D . P A 2
H9B H 0.922200 0.901224 0.513029 0.031 Uiso 0.301(2) 1 calc R U P A 2
C10 C 0.78187(11) 0.31144(11) 0.42453(12) 0.0246(2) Uani 1 1 d . . . . .
H10 H 0.763790 0.345880 0.499467 0.030 Uiso 1 1 calc R U . . .
C11 C 0.67864(12) 0.33074(12) 0.34747(12) 0.0262(3) Uani 1 1 d . . . . .
C12 C 0.66612(14) 0.26926(15) 0.24666(13) 0.0352(3) Uani 1 1 d . . . . .
H12 H 0.719257 0.210059 0.227557 0.042 Uiso 1 1 calc R U . . .
C13 C 0.57585(15) 0.29451(17) 0.17397(15) 0.0420(4) Uani 1 1 d . . . . .
H13 H 0.567909 0.251772 0.105855 0.050 Uiso 1 1 calc R U . . .
C14 C 0.49703(14) 0.38146(16) 0.19961(15) 0.0412(4) Uani 1 1 d . . . . .
C15 C 0.50944(13) 0.44042(14) 0.30048(16) 0.0377(4) Uani 1 1 d . . . . .
H15 H 0.455849 0.499028 0.320013 0.045 Uiso 1 1 calc R U . . .
C16 C 0.59884(12) 0.41559(13) 0.37391(14) 0.0309(3) Uani 1 1 d . . . . .
H16 H 0.605326 0.457135 0.442833 0.037 Uiso 1 1 calc R U . . .
C17 C 0.40087(18) 0.4109(2) 0.1195(2) 0.0629(6) Uani 1 1 d . . . . .
H17A H 0.430818 0.453187 0.054580 0.094 Uiso 0.55(3) 1 calc R U P B 1
H17B H 0.345297 0.460216 0.157854 0.094 Uiso 0.55(3) 1 calc R U P B 1
H17C H 0.364148 0.338332 0.094067 0.094 Uiso 0.55(3) 1 calc R U P B 1
H17D H 0.329722 0.379120 0.148579 0.094 Uiso 0.45(3) 1 calc R U P B 2
H17E H 0.416065 0.376368 0.045795 0.094 Uiso 0.45(3) 1 calc R U P B 2
H17F H 0.394476 0.496246 0.112127 0.094 Uiso 0.45(3) 1 calc R U P B 2
C18 C 0.81263(13) 0.18305(12) 0.44276(13) 0.0301(3) Uani 1 1 d . . . . .
H18A H 0.747251 0.141290 0.473500 0.045 Uiso 1 1 calc R U . . .
H18B H 0.876757 0.177586 0.495563 0.045 Uiso 1 1 calc R U . . .
H18C H 0.833681 0.147669 0.370934 0.045 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.3608(16) . ?
N1 N2 1.3626(15) . ?
N1 C2 1.3884(17) . ?
N2 C1 1.3390(17) . ?
C1 N3 1.3622(18) . ?
C1 C6B 1.452(2) . ?
C1 C6A 1.4522(19) . ?
N3 C2 1.3350(17) . ?
C2 N4 1.3429(17) . ?
N4 C3 1.3255(18) . ?
C3 C4 1.4101(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3705(19) . ?
C4 H4 0.9500 . ?
C5 C10 1.5110(18) . ?
C6A C9A 1.324(6) . ?
C6A S1A 1.736(3) . ?
S1A C7A 1.720(3) . ?
C7A C8A 1.360(3) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.446(9) . ?
C8A H8A 0.9500 . ?
C9A H9A 0.9500 . ?
C6B C9B 1.324(6) . ?
C6B S1B 1.736(3) . ?
S1B C7B 1.720(3) . ?
C7B C8B 1.359(3) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.419(15) . ?
C8B H8B 0.9500 . ?
C9B H9B 0.9500 . ?
C10 C18 1.5230(18) . ?
C10 C11 1.5320(19) . ?
C10 H10 1.0000 . ?
C11 C16 1.388(2) . ?
C11 C12 1.397(2) . ?
C12 C13 1.394(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 C17 1.511(2) . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17D 0.9800 . ?
C17 H17E 0.9800 . ?
C17 H17F 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 N2 126.52(11) . . ?
C5 N1 C2 123.47(11) . . ?
N2 N1 C2 110.01(10) . . ?
C1 N2 N1 101.59(10) . . ?
N2 C1 N3 116.40(12) . . ?
N2 C1 C6B 125.0(3) . . ?
N3 C1 C6B 118.5(3) . . ?
N2 C1 C6A 117.83(19) . . ?
N3 C1 C6A 125.71(19) . . ?
C2 N3 C1 102.71(11) . . ?
N3 C2 N4 128.68(12) . . ?
N3 C2 N1 109.29(11) . . ?
N4 C2 N1 122.03(12) . . ?
C3 N4 C2 114.96(12) . . ?
N4 C3 C4 125.10(13) . . ?
N4 C3 H3 117.5 . . ?
C4 C3 H3 117.5 . . ?
C5 C4 C3 119.60(12) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 114.85(12) . . ?
N1 C5 C10 117.47(11) . . ?
C4 C5 C10 127.58(12) . . ?
C9A C6A C1 128.4(5) . . ?
C9A C6A S1A 111.5(5) . . ?
C1 C6A S1A 120.0(2) . . ?
C7A S1A C6A 91.14(16) . . ?
C8A C7A S1A 112.5(4) . . ?
C8A C7A H7A 123.8 . . ?
S1A C7A H7A 123.8 . . ?
C7A C8A C9A 110.7(5) . . ?
C7A C8A H8A 124.7 . . ?
C9A C8A H8A 124.7 . . ?
C6A C9A C8A 114.1(7) . . ?
C6A C9A H9A 123.0 . . ?
C8A C9A H9A 123.0 . . ?
C9B C6B C1 132.2(8) . . ?
C9B C6B S1B 112.6(6) . . ?
C1 C6B S1B 114.2(3) . . ?
C7B S1B C6B 89.8(4) . . ?
C8B C7B S1B 112.4(9) . . ?
C8B C7B H7B 123.8 . . ?
S1B C7B H7B 123.8 . . ?
C7B C8B C9B 111.7(10) . . ?
C7B C8B H8B 124.2 . . ?
C9B C8B H8B 124.2 . . ?
C6B C9B C8B 113.0(9) . . ?
C6B C9B H9B 123.5 . . ?
C8B C9B H9B 123.5 . . ?
C5 C10 C18 112.74(11) . . ?
C5 C10 C11 106.74(10) . . ?
C18 C10 C11 114.18(11) . . ?
C5 C10 H10 107.6 . . ?
C18 C10 H10 107.6 . . ?
C11 C10 H10 107.6 . . ?
C16 C11 C12 118.63(13) . . ?
C16 C11 C10 119.99(13) . . ?
C12 C11 C10 121.26(13) . . ?
C13 C12 C11 120.20(16) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 121.08(16) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 118.12(15) . . ?
C15 C14 C17 120.81(19) . . ?
C13 C14 C17 121.08(19) . . ?
C14 C15 C16 121.30(16) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C11 C16 C15 120.65(15) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C17 H17D 109.5 . . ?
C14 C17 H17E 109.5 . . ?
H17D C17 H17E 109.5 . . ?
C14 C17 H17F 109.5 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 C1 179.70(12) . . . . ?
C2 N1 N2 C1 -0.13(13) . . . . ?
N1 N2 C1 N3 0.04(14) . . . . ?
N1 N2 C1 C6B 177.7(11) . . . . ?
N1 N2 C1 C6A -177.3(4) . . . . ?
N2 C1 N3 C2 0.07(15) . . . . ?
C6B C1 N3 C2 -177.7(10) . . . . ?
C6A C1 N3 C2 177.2(4) . . . . ?
C1 N3 C2 N4 179.82(13) . . . . ?
C1 N3 C2 N1 -0.15(13) . . . . ?
C5 N1 C2 N3 -179.65(11) . . . . ?
N2 N1 C2 N3 0.19(14) . . . . ?
C5 N1 C2 N4 0.38(19) . . . . ?
N2 N1 C2 N4 -179.78(11) . . . . ?
N3 C2 N4 C3 179.88(13) . . . . ?
N1 C2 N4 C3 -0.15(18) . . . . ?
C2 N4 C3 C4 0.0(2) . . . . ?
N4 C3 C4 C5 0.0(2) . . . . ?
N2 N1 C5 C4 179.83(11) . . . . ?
C2 N1 C5 C4 -0.36(17) . . . . ?
N2 N1 C5 C10 3.37(18) . . . . ?
C2 N1 C5 C10 -176.82(11) . . . . ?
C3 C4 C5 N1 0.16(18) . . . . ?
C3 C4 C5 C10 176.20(12) . . . . ?
N2 C1 C6A C9A -0.6(11) . . . . ?
N3 C1 C6A C9A -177.7(8) . . . . ?
N2 C1 C6A S1A -175.8(4) . . . . ?
N3 C1 C6A S1A 7.1(8) . . . . ?
C9A C6A S1A C7A 2.1(8) . . . . ?
C1 C6A S1A C7A 178.2(6) . . . . ?
C6A S1A C7A C8A 0.3(5) . . . . ?
S1A C7A C8A C9A -2.5(7) . . . . ?
C1 C6A C9A C8A -179.6(7) . . . . ?
S1A C6A C9A C8A -4.0(11) . . . . ?
C7A C8A C9A C6A 4.2(11) . . . . ?
N2 C1 C6B C9B 175.0(16) . . . . ?
N3 C1 C6B C9B -7(3) . . . . ?
N2 C1 C6B S1B 7.6(19) . . . . ?
N3 C1 C6B S1B -174.8(8) . . . . ?
C9B C6B S1B C7B 6.7(16) . . . . ?
C1 C6B S1B C7B 176.6(14) . . . . ?
C6B S1B C7B C8B -4.8(14) . . . . ?
S1B C7B C8B C9B 2.0(16) . . . . ?
C1 C6B C9B C8B -174.4(17) . . . . ?
S1B C6B C9B C8B -6.8(19) . . . . ?
C7B C8B C9B C6B 3.1(19) . . . . ?
N1 C5 C10 C18 -148.09(12) . . . . ?
C4 C5 C10 C18 35.97(18) . . . . ?
N1 C5 C10 C11 85.76(14) . . . . ?
C4 C5 C10 C11 -90.19(15) . . . . ?
C5 C10 C11 C16 -95.99(15) . . . . ?
C18 C10 C11 C16 138.72(14) . . . . ?
C5 C10 C11 C12 80.10(16) . . . . ?
C18 C10 C11 C12 -45.19(18) . . . . ?
C16 C11 C12 C13 0.9(2) . . . . ?
C10 C11 C12 C13 -175.25(14) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
C12 C13 C14 C17 178.47(17) . . . . ?
C13 C14 C15 C16 1.1(2) . . . . ?
C17 C14 C15 C16 -178.78(16) . . . . ?
C12 C11 C16 C15 -1.2(2) . . . . ?
C10 C11 C16 C15 174.99(13) . . . . ?
C14 C15 C16 C11 0.2(2) . . . . ?

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.063



_exptl_crystal_recrystallization_method 'Vapour deposition'
